After a respectable debut in Asian football's premier club competition last year, where they picked up two wins and a draw from six games, the current campaign offered the ambitious Singapore Premier League outfit -- founded just three years ago -- another chance to prove they can match it with the continent's best.
The clearest indication of the Sailors' intent came in their recruitment.
Domestically, the SPL only allows four imports.
However, with the ACL's limit being six foreign players on the field at any time in a game, and no limit on the number that can be registered in a team's 35-man squad, the Sailors were certainly willing to put in additional investment for their continental challenge.
At present, their squad boasts eight foreigners -- and none, imaginably, would have come on the cheap.
Others, like Rui Pires, were brought in during the mid-year window solely to feature in the ACL.
This willingness to cater separate -- and extra -- resources for their Asian campaign has provided Lion City with additional experience and depth for the undeniably tougher tests than the ones they mostly come up against on the local front.
On Wednesday, even with Australia international Bailey Wright and Brazilian playmaker Diego Lopes absent, the Sailors started with five foreigners against Jeonbuk Hyundai Motors -- and were even able to bring on Tanaka, who has just recovered from a serious injury that ruled him out for most of this year, late in the contest.
And it was one of those among them who came up with the goods as LCS claimed their biggest win in the ACL yet as they downed the South Korean giants and two-time Asian champions with an impressive 2-0 win.
Richairo Zivkovic was brought into the club in the middle of the domestic campaign as a replacement for Tanaka and, while he ultimately netted on six occasions, he was unable to help the Sailors pip Albirex Niigata (S) to the title.
But it was also expected that Zivkovic's wealth of experience could also come in handy in the ACL.
Once a highly-rated prospect coming through Ajax's famed academy, the 27-year-old has since embarked on a well-travelled career that has taken him to China and Serbia -- but also to the Premier League during a loan spell with Sheffield United -- before he found his way to Singapore.
On Wednesday, with two emphatic finishes after being set up brilliantly by Shawal Anuar on both occasions, Zivkovic secured for the Sailors a triumph that will go down in the club's history books.
Lion City's first-ever victory in the competition -- last season's 3-0 win over another South Korean team in Daegu FC -- was equally impressive and monumental.
Yet, with all due respect to Daegu, Jeonbuk are a far different proposition both in terms of history and reputation, even if the two teams may now be operating at similar levels on the playing field.
Unfortunately for Zivkovic and the Sailors, they might not have many more evenings like this to savour -- at least for the immediate future.
With Asian club football undergoing a revamp next season, the top-tier competition -- which will be known as the AFC Champions League Elite moving forward -- will be reduced to just 24 teams from the Asian Football Confederation's leading nations.
Based on their current ranking in the confederation's club competition rankings, Singapore will not feature in that competition but will instead have to settle for the second-tier AFC Champions League 2 until they fare well enough to climb up the standings.
Currently sitting level in second place on six points with Jeonbuk in Group F, the Sailors have at least two more to look forward to -- against leaders Bangkok United and Kitchee on Nov. 29 and Dec. 13 respectively.
Produce similar displays to the one they had against Jeonbuk and they could just buy themselves a couple more with a maiden appearance in the knockout round.
Either way, as the Sailors prepare to say goodbye to the top level of Asian football at least for awhile once their current campaign concludes, they will always have Wednesday's stunning win over the mighty Jeonbuk to look back on.
Thanks to having a forward-thinking and ambitious approach to competing in the ACL, and a Curaçoan journeyman who came good when it mattered the most.